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Knowing exactly when to make your move is sometimes more
difficult than knowing what your move should be.

That San Francisco-based peer-to-peer ridesharing app Lyft would move into
New York City is hardly a question. The Big Apple is the largest
city in the United States where a huge swath of the population
lives without owning a car.

Whether Lyft entered New York City at the right time, however?
That’s debatable.

In celebration of its soft launch, Lyft offered its "Pioneers" --
the ridesharing company’s name for its first users -- two weeks
of free rides on its service. “Hundreds” of drivers completed
“thousands” of rides over the first weekend, according to Lyft.
Exact numbers were not disclosed.

The facts: The Lyft launch was late, an amended version of what
it initially had promised, and left would-be riders unable to get
a ride when they wanted one.

Should the West Coast car-sharing app have waited a bit longer
before launching in New York? Perhaps with more time, Lyft could
have had the regulations already worked out and had more drivers
ready to go. Or is a bumpy launch part of the game when you are
bringing a new, innovative technology to a huge market with
existing stakeholders firmly wedded to the status quo?

The answer to both of those questions, depending, of course on
who you ask, is yes.

The key, though, is being able to move quickly and adjust to
unforeseen circumstances when they come up. Schroeder says that
while Lyft may very well have been prepared to enter its largest
potential market yet, it still underestimated the complexities of
working in New York City. The political infrastructure of New
York, the regulators, the existing taxi services are all very
entrenched in the Big Apple. What works in Chicago won't
necessarily just scale to work in New York, Schroeder says.

It’s easy to fault Lyft for being unprepared. But it’s also true
that if Lyft waited for New York City regulators and drivers to
welcome them with open arms, the San Francisco company may have
never entered New York City.

Entrepreneurs whose business success depends on regulators
embracing new rules and individuals adopting new social norms
(your mom did tell you growing up to never get into a
car with a stranger, right?) can’t always wait for perfect.
Airbnb, the peer-to-peer apartment-rental site that is no
stranger to legal battles and skeptics, would never have launched
had its founders waited for everything to fall into place,
co-founder
Nathan Blecharczyk has said. He believes that with any new
technology comes resistance, and the only way to force change is
to jump in the deep end.

One way Lyft could have minimized some of the frustrations it has
caused in New York City is to have launched more slowly, says
Schroeder. Inviting a small number of people to initially use the
service could have given Lyft the opportunity to quietly
stress-test the technology and then roll it out over a month or
longer. Launching “shotgun”-style in a massive, complex market
like New York City may not have been the best plan, he says.

What really matters now is what Lyft does going forward. With
competitor Uber already positioned to capitalize on Lyft's fumble
in New York City, Lyft’s best play may well be a mea
culpa. The company could even put a positive spin on its
shortage of drivers, saying its service was more popular than
expected. "The market is forgiving of this type of faux
pas -- if you recover properly and correct your problems
quickly enough.”

Launching early and then backstepping, admitting to your
customers that you may have been trigger happy is a classic Mark
Zuckerberg move, notes
Tony Marino, a business expansion strategist. The reason
Zuckerberg gets away with boldly charging ahead is that Facebook
is transparent and apologetic when it does get ahead of itself.
“I think the company can make lemonade out of lemons,” he says.
“People love to hear 'I am sorry.'”

Lyft is taking steps to make amends with customers. It has
assured its Pioneer riders who haven’t been able to get a rides
in New York City that it will re-issue their two weeks of free
rides, and says it is working to get more drivers as fast as
possible.

According to Lyft, the hurdles it has faced in New York City so
far are not exceptionally out of the ordinary, nor are they deal
breakers. “We have encountered challenges before and we have
always been able to find a path forward through conversations
with regulators,” said Erin Simpson, the company's director of
communications. “We are confident that we will have a path
forward.”

That may be so, but time is of the essence for Lyft to get back
in New Yorkers' good graces. “This is a chess match -- a
high-speed chess match,” says Schroeder.